Humor has been positively perceived in general. However, research has shown that a leader should adopt humor with care and only after considering the relevant context, such as cultural differences. This study was undertaken to gain insight into how leader humor is perceived in the predominantly Confucian culture of Taiwan, through a series of in-depth interviews with individuals from throughout the hierarchies of various organizations. Overall, our participants expressed conflicting attitudes toward leader humor in the workplace, depending on the place and time of their leader humor experience. Specifically, leader humor was deemed more effective in informal domains and when a good leader–follower relationship exists. The findings echo the implicit theory of leadership and highlight the need to consider the context when exercising leader humor in Confucian cultures. Implications and future study directions are discussed.